US5354735A - Use of a cyclopentadecenone as perfuming ingredient - Google Patents
Use of a cyclopentadecenone as perfuming ingredient Download PDFInfo
- Publication number
- US5354735A US5354735A US08/082,214 US8221493A US5354735A US 5354735 A US5354735 A US 5354735A US 8221493 A US8221493 A US 8221493A US 5354735 A US5354735 A US 5354735A
- Authority
- US
- United States
- Prior art keywords
- methyl
- cyclopentadec
- composition
- article
- perfuming
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
Definitions
- the present invention relates to the field of perfumery. It concerns, more particularly, a method to confer, improve, enhance or modify the odor properties of a perfuming composition or a perfumed article, which method comprises adding to said composition or article a fragrance effective amount of 3-methyl-cyclopentadec-5-en-1-one.
- the invention also concerns a perfuming composition or a perfumed article containing 3-methyl-cyclopentadec-5-en-1-one as active perfuming ingredient.
- Another object of the invention is a composition containing 3-methyl-cyclopentadec-5-en-1-one and 3-methyl-cyclopentadec-4-en-1-one, and wherein the weight proportion of 3-methyl-cyclopentadec-5-en-1-one is equal to 70% or more.
- the invention further provides a method of use of this latter composition in perfumery.
- 3-Methyl-cyclopentadec-5-en-1-one is a macrocyclic ketone and an unsaturated homolog of muscone, a compound which is well appreciated in perfumery. Owing to the presence of a ring double bond, there are several possible position and configuration isomers for this molecule. The structure of some of them is known. Thus, the structure of the above-mentioned enone, as well as that of several of its isomers, has been described in the literature, mostly in connection with organic syntheses, namely that of muscone. However, there has been no mention of any possible useful odor properties for these compounds.
- ketones (I), or mixtures of ketones (I), are cited in said patent, namely 3-methyl-cis-cyclopentadec-4-en-1-one (example 4) and 3-methyl-trans-cyclopentadec-4-en-1-one (example 17), as well as a mixture containing essentially the trans isomers of 3-methyl-cyclopentadec-4 and 5-en-1-one (examples 1 et 2), we were unable to find any description of the individual properties of any of these ketones or mixtures, or of the possible olfactive differences between them.
- patent describes either mixtures of isomers, containing both 3-methyl-cyclopentadec-5-en-1-one and 3-methyl-cyclopentadec-4-en-1-one, or the cis isomer of the latter, while patent GB 2 058 786 only describes the preparation of 3-methyl-cyclopentadec-4-en-1-one without specifying any isomeric proportions.
- 3-methyl-cydopentadec-5-en-1-one, and its cis and trans isomers are equally convenient for fine perfumery and technical perfumery applications.
- Their tenacity on textiles renders them particularly useful for perfuming laundry detergents and fabric softeners. In these applications, they can be used on their own or in admixture with other perfuming ingredients, solvents or adjuvants of current use in the art.
- proportions in which these compounds can be used depend on the fragrance effect that one desires to achieve, as well as on the nature of the other perfuming co-ingredients in a given composition.
- concentrations of the order of 5 to 10%, or even 20% or more by weight, relative to the weight of the perfuming composition or perfume into which they are incorporated.
- a base perfuming composition was prepared by admixing the following ingredients:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH239592 | 1992-07-30 | ||
CH2395/92 | 1992-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5354735A true US5354735A (en) | 1994-10-11 |
Family
ID=4232775
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/082,214 Expired - Lifetime US5354735A (en) | 1992-07-30 | 1993-06-24 | Use of a cyclopentadecenone as perfuming ingredient |
Country Status (4)
Country | Link |
---|---|
US (1) | US5354735A (fr) |
EP (1) | EP0584477B1 (fr) |
JP (1) | JP3609845B2 (fr) |
DE (1) | DE69314121T2 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5679634A (en) * | 1994-05-09 | 1997-10-21 | Firmenich S.A. | Use of dihydrobenzofuranones as perfuming ingredients |
US5792740A (en) * | 1996-03-08 | 1998-08-11 | Firmenich Sa | Fragrant macrocyclic lactones |
US6200254B1 (en) * | 1999-05-21 | 2001-03-13 | Takasago International Corporation | Macrocyclic ketones as fragrance materials and methods for making same |
US6326349B1 (en) | 1998-09-03 | 2001-12-04 | Givaudan Roure (International) Sa | Methylcyclotetradec-5-en-1-ones |
US7030079B1 (en) | 2000-07-06 | 2006-04-18 | Fragrance Resources, Inc. | Fragrance composition exhibiting varying olfactive characteristics when applied on different persons |
WO2015107017A1 (fr) * | 2014-01-14 | 2015-07-23 | Firmenich Sa | Macrocycles poudreux à odeur musquée |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4495313B2 (ja) * | 2000-07-13 | 2010-07-07 | 長谷川香料株式会社 | 光学活性3−メチル−5−シクロペンタデセン−1−オンの製法および新規中間体 |
EP2665715B1 (fr) | 2011-01-18 | 2014-11-26 | Firmenich SA | Macrocycles spiroépoxy en tant qu'ingrédients parfumants |
US10196332B2 (en) * | 2015-09-22 | 2019-02-05 | Basf Se | Process for preparing 3-methylcyclopentadecane-1,5-diol |
EP3170828A1 (fr) * | 2015-11-23 | 2017-05-24 | Basf Se | Procede de preparation de composes a squelette de 16-oxabicycloo[10.3.1]pentadecen et leurs produits secondaires |
BR112018077067B1 (pt) * | 2016-07-15 | 2022-05-31 | Basf Se | Processo para preparar um composto |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1558413A (fr) * | 1966-12-08 | 1969-02-28 | ||
JPS5242787A (en) * | 1975-09-30 | 1977-04-02 | Shimadzu Corp | Device for preparation of section scintigram |
JPS5512408A (en) * | 1978-07-12 | 1980-01-29 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Breakdown voltage testing method of insulator |
EP0025869A1 (fr) * | 1979-08-28 | 1981-04-01 | Haarmann & Reimer Gmbh | 3-Méthyl-cyclohexadécén-5-one-1, procédé pour sa préparation et son utilisation comme matière odorante |
GB2058786A (en) * | 1979-09-13 | 1981-04-15 | Firmenich & Cie | Process for the preparation of muscone and muscenone 16-oxa-3-methyl (10.3.1) pentadec-1-ene |
US4346023A (en) * | 1979-09-19 | 1982-08-24 | Firmenich Sa | Process for the preparation of novel unsaturated macrocyclic ketones |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4302607A (en) * | 1979-02-12 | 1981-11-24 | Firmenich Sa | Process for the preparation of novel unsaturated macrocyclic ketones |
-
1993
- 1993-06-17 EP EP93109656A patent/EP0584477B1/fr not_active Expired - Lifetime
- 1993-06-17 DE DE69314121T patent/DE69314121T2/de not_active Expired - Lifetime
- 1993-06-24 US US08/082,214 patent/US5354735A/en not_active Expired - Lifetime
- 1993-07-28 JP JP18600793A patent/JP3609845B2/ja not_active Expired - Lifetime
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1558413A (fr) * | 1966-12-08 | 1969-02-28 | ||
US3778483A (en) * | 1966-12-08 | 1973-12-11 | Firmenich & Cie | Methods for the manufacture of macrocyclic compounds |
JPS5242787A (en) * | 1975-09-30 | 1977-04-02 | Shimadzu Corp | Device for preparation of section scintigram |
JPS5512408A (en) * | 1978-07-12 | 1980-01-29 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Breakdown voltage testing method of insulator |
EP0025869A1 (fr) * | 1979-08-28 | 1981-04-01 | Haarmann & Reimer Gmbh | 3-Méthyl-cyclohexadécén-5-one-1, procédé pour sa préparation et son utilisation comme matière odorante |
GB2058786A (en) * | 1979-09-13 | 1981-04-15 | Firmenich & Cie | Process for the preparation of muscone and muscenone 16-oxa-3-methyl (10.3.1) pentadec-1-ene |
US4480107A (en) * | 1979-09-13 | 1984-10-30 | Firmenich Sa | Pyranic derivatives useful as intermediates in making muscone |
US4346023A (en) * | 1979-09-19 | 1982-08-24 | Firmenich Sa | Process for the preparation of novel unsaturated macrocyclic ketones |
Non-Patent Citations (1)
Title |
---|
S. Arctander, Perfume and Flavor Chemicals, Sections 1214, 1985, 2278, 2279 (1969). * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5679634A (en) * | 1994-05-09 | 1997-10-21 | Firmenich S.A. | Use of dihydrobenzofuranones as perfuming ingredients |
US5792740A (en) * | 1996-03-08 | 1998-08-11 | Firmenich Sa | Fragrant macrocyclic lactones |
USRE36493E (en) * | 1996-03-08 | 2000-01-11 | Firmenich Sa | Fragrant macrocyclic lactones |
US6326349B1 (en) | 1998-09-03 | 2001-12-04 | Givaudan Roure (International) Sa | Methylcyclotetradec-5-en-1-ones |
CN1113842C (zh) * | 1998-09-03 | 2003-07-09 | 吉沃丹·鲁里国际公司 | 甲基环十四-5-烯-1-酮 |
US6200254B1 (en) * | 1999-05-21 | 2001-03-13 | Takasago International Corporation | Macrocyclic ketones as fragrance materials and methods for making same |
US7030079B1 (en) | 2000-07-06 | 2006-04-18 | Fragrance Resources, Inc. | Fragrance composition exhibiting varying olfactive characteristics when applied on different persons |
WO2015107017A1 (fr) * | 2014-01-14 | 2015-07-23 | Firmenich Sa | Macrocycles poudreux à odeur musquée |
US20160340606A1 (en) * | 2014-01-14 | 2016-11-24 | Firmenich Sa | Powdery, musky odorant macrocycles |
US9896644B2 (en) * | 2014-01-14 | 2018-02-20 | Firmenich Sa | Powdery, musky odorant macrocycles |
Also Published As
Publication number | Publication date |
---|---|
DE69314121T2 (de) | 1998-02-26 |
EP0584477A1 (fr) | 1994-03-02 |
JPH06192680A (ja) | 1994-07-12 |
EP0584477B1 (fr) | 1997-09-24 |
DE69314121D1 (de) | 1997-10-30 |
JP3609845B2 (ja) | 2005-01-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6737396B2 (en) | Use of (1-ethoxyethoxy)cyclododecane in a perfume composition as perfume fixative and/or enhancer | |
MXPA06005893A (es) | Compuestos fragantes de almizcle. | |
US5354735A (en) | Use of a cyclopentadecenone as perfuming ingredient | |
US5266559A (en) | Use of unsaturated macrocyclic lactones as perfuming ingredients | |
JP3040449B2 (ja) | 芳香特性の賦与、改良、強化又は変性法、香料組成物及び芳香製品 | |
US4671798A (en) | 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-1-naphthalenol, its use as perfuming ingredient and process for making same | |
EP1904612B1 (fr) | Ingrédients de parfum de type boisé | |
US5155095A (en) | Fragrance ingredient | |
US5219836A (en) | Use of tetrahydro-4-methyl-2-phenyl-2H-pyran as perfuming ingredient | |
US5538943A (en) | Use of 1,3-undecadien-5-yne as a perfuming ingredient | |
IL205805A (en) | Patchoulol odorant | |
US4514323A (en) | Utilization of 2-hydroxy-3,4,4-trimethyl-cyclopent-2-en-1-one as perfuming ingredient | |
US7115552B2 (en) | Spiroepoxy-macrocycle as perfuming ingredient | |
US5814598A (en) | Use of unsaturated aliphatic esters in perfumery | |
US6872697B2 (en) | Oxime as perfuming ingredient | |
EP1776329B1 (fr) | Citronnelle et ingredient de parfum floral | |
US9284513B2 (en) | Sage odorant | |
US4661286A (en) | Oxaspirododecane derivatives and perfume compositions containing them | |
US4717771A (en) | Unsaturated aliphatic ketone [and use of same as perfuming ingredient] | |
EP2622051A1 (fr) | Dérivés 4,4-diméthyl-décal-1-one ou -1-ol comme ingrédients de parfum | |
US5151410A (en) | Use of a spiranic compound as a perfuming ingredient | |
US7494968B2 (en) | Non-cyclic hindered ketones as perfuming ingredient | |
WO2005110961A1 (fr) | Cetones non cycliques entraves en tant qu'ingredient de parfumerie | |
MX2014001544A (es) | Odorantes de hojas de violeta. | |
WO2012045608A1 (fr) | Alcools odorants |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: FIRMENICH SA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:DEMOLE, EDOUARD;MAHAIM, CYRIL;BLANC, PIERRE-ALAIN;REEL/FRAME:006594/0870 Effective date: 19930609 |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: APPLICATION UNDERGOING PREEXAM PROCESSING |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
FPAY | Fee payment |
Year of fee payment: 12 |